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Issue 31, 2018
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Regioselectivity of the Pauson–Khand reaction in single-walled carbon nanotubes

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Abstract

Chemical functionalization of nanotubes, in which their properties can be combined with those of other classes of materials, is fundamental to improve the physicochemical properties of nanotubes for potential technological applications. In this work, we theoretically and experimentally examine the Pauson–Khand reaction (PKR) on zig-zag, armchair, and chiral single-walled carbon nanotubes (SWCNTs). Our benchmarked density functional theory (DFT) calculations show that an alternative pathway to the widely accepted Magnus reaction pathway has significantly lower energy barriers, thus suggesting the use of this alternative pathway to predict whether a PKR on SWCNTs is favored or hampered. Accessible energy barriers of up to 16 kcal mol−1 are estimated and our results suggest that semiconducting SWCNTs react faster than metallic ones, although both types can be functionalized. Guided by our theoretical predictions, cyclopentenones are successfully attached to SWCNTs by heating and are, subsequently, characterized in the laboratory.

Graphical abstract: Regioselectivity of the Pauson–Khand reaction in single-walled carbon nanotubes

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Publication details

The article was received on 28 Apr 2018, accepted on 20 Jul 2018 and first published on 25 Jul 2018


Article type: Paper
DOI: 10.1039/C8NR03480J
Citation: Nanoscale, 2018,10, 15078-15089
  • Open access: Creative Commons BY license
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    Regioselectivity of the Pauson–Khand reaction in single-walled carbon nanotubes

    J. P. Martínez, M. Vizuete, L. M. Arellano, A. Poater, F. M. Bickelhaupt, F. Langa and M. Solà, Nanoscale, 2018, 10, 15078
    DOI: 10.1039/C8NR03480J

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